title: A stereoselective approach to γ-functionalized carbonyls exploiting the Cu-promoted S(N)2' reaction.
abstract: While several efficient processes exist to effect the stereoselective creation of carbon-carbon bonds in the α- and β-position of carbonyls, functionalization of the γ-position is much more challenging. We disclose an alternative methodology exploiting the Cu-promoted S(N)2' reaction to achieve the addition of various nucleophiles upon the allylic lactones 5a-d which lead to the generation of the desired γ-functionalized α,β-unsaturated aldehydes 6 following in situ hydrolysis.
authors.affiliation: Department of Medicinal Chemistry, Merck Frosst Canada Inc., 16711 Trans Canada Highway, Kirkland, Québec, H9H 3L1, Canada.
authors.forename: Eric
authors.initials: E
authors.lastname: Bond
authors.forename: Anne-Marie
authors.initials: AM
authors.lastname: Beausoleil
authors.forename: Jennifer
authors.initials: J
authors.lastname: Howell
authors.forename: Alicia
authors.initials: A
authors.lastname: Wong
authors.forename: Joël
authors.initials: J
authors.lastname: Robichaud
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000478:Alkylation; D002244:Carbon / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006868:Hydrolysis; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D007783:Lactones; D002244:Carbon; D003300:Copper